Old Union Town Hall // 1847

Union, Connecticut is the smallest (by population) town in the state and it was the last Connecticut town east of the Connecticut River to be settled, largely because of its rough terrain and poor soil. The small town of under 800 residents was incorporated in 1734 and named Union, likely named after the fact that the new town was formed of a “union” of different sections of land which were left over when the boundaries of surrounding towns, though it is still speculation. Union erected this Town Hall building in 1847 which was fitting for the town’s small (and then-declining) population at the time. The one-story clapboard building is vernacular and lacks much adornment of other town halls and institutional buildings of the time period in nearby towns. Eventually, the town built a new city offices building and the small town continues to maintain the former building to this day and it houses the Union Historical Society.

Overlook Mansion // 1882

Raised in an intellectual home of his widowed father, William Allen Jenner (1844-1915) graduated from Middlebury College as the youngest in his class with highest honors. He would go on to graduate from Columbia Law School and be admitted to the New York Bar in 1867, becoming a partner in a prestigious New York City law firm. Outside of practicing law, William Jenner studied and authored textbooks on the Latin language and was an avid horticulturalist. His landscape architecture passion was fulfilled when he purchased a large house lot on High Ridge Road in Ridgefield Connecticut, and built this home in 1882, named “Overlook”, where he and his family would spend their summers outside of the city. Mr. Jenner and his wife, Josephine Curtis Jenner, raised three daughters between New York and Ridgefield. One of their daughters, Anna, would marry Sterling Foote, a New York City cotton broker. The Foote’s would inherit Overlook and spend their summers here until their death. The Queen Anne/Shingle style mansion showcases the shift of Ridgefield from sleepy farming town to summer destination for wealthy New York residents, a trend which continues to this day.

“Good Cheer Estate” // c.1820

Originally built as a Federal period farmhouse, this gorgeous estate is the epitome of what happened to Ridgefield… city money! By the end of the 19th century, wealthy New Yorkers were flocking to small towns every summer for clean air, rest, and relaxation. Ridgefield, Connecticut became an obvious option for its close proximity to New York and bucolic setting of farmlands bounded by old stone and rolling hills. As a result, wealthy summer residents purchased older estates and either demolished or renovated the homes there. Aaron Lockwood Northrop was raised in Ridgefield and was educated in its private schools before moving to New York as a young man, being awarded an apprenticeship as a dentist. Dr. Northrop went on to establish a prominent dental practice and would serve as President of the American Dental Association. As a wealthy adult, he acquired a circa 1820 house on this lot and renovated it, doubling its size and giving the residence its current Victorian flair. The summer house was affectionately named “Good Cheer”. Aaron died unexpectedly in 1908 while overseas in Paris, France. His widow, Caroline, resided at Good Cheer until her own death in 1927.

Maynard Estate // 1901

One of the largest summer estates in Ridgefield is this Neoclassical residence on Peaceable Street, which was built in 1901 for Effingham Maynard and his wife Helen. Maynard was a partner in Clark & Maynard, a New York publishing house. Local lore states that the Maynard Family hired New York architect Stanford White, to design this property, but no definitive proof could be located to substantiate that rumor. The Olmsted Brothers landscape architecture firm designed the grounds which were elaborate with gardens and outbuildings. The two unmarried Maynard daughters, Mary and Helen spent their summers here every year until their deaths in the 1950s.

Branchville Railroad Tenement // c.1853

The Branchville Railroad Tenement in Ridgefield, Connecticut was built in three phases between around 1853 and 1905 and is one of the towns significant vernacular landmarks. Its earliest incarnation was as a storage facility for the railroad station, to which two stories of residences were added to houses workers on the railroad. Following completion of the railroad, the building was converted into a hotel in 1880, at which time the two-story porch was built and the interior was redecorated. This was apparently an unsuccessful venture, and in 1905 it was converted to a saloon and multifamily residence. Today, the old railroad tenement is home to a small business with housing above.

Ashton Croft Mansion and Carriage House // c.1892

Tucked behind the Jesse Lee Memorial Church on Main Street in Ridgefield, you will find this stately Queen Anne/Tudor Revival estate. The ‘Ashton Croft’ Manor House, now called Wesley Hall, is part of the Jesse Lee Memorial United Methodist Church complex and it has been modified several times blending two distinct styles into a single, pleasing composition. This house was originally constructed by Henry and Elizabeth Hawley circa 1892 in the Queen Anne style. The house was later sold to Electa Matilda Ziegler, a wealthy New York City widow in 1912, who reconfigured the structure to include half-timbering on the gables and upper story walls in the Tudor Revival style. She spent summers at a mansion in Darien, Connecticut, and would sell her Ridgefield property to Sanford H.E. Freund, a New York City attorney. The local order of Odd Fellows bought the estate from the Freund family in 1956. Three years later, the organization sold most of the property — retaining the carriage house for its lodge — to Jesse Lee Methodist Church, which planned to eventually build a new church there to replace the old one at Main and Catoonah Streets. Today, the entire former Ashton Croft estate is owned by the local Methodist Church and is known as Wesley Hall.

Jesse Lee Memorial Church // 1965

Believe it or not, this church in Ridgefield Center was built in 1965! To know its full history, we have to go back to 1787, when the Methodist Episcopal Church had its beginnings in Ridgefield, the third in New England. Its first meeting was held – just 21 years after Methodism had been introduced into the U.S. from England. In 1789 Jesse Lee, a native of Virginia, was sent north as a circuit rider. His third sermon in Connecticut was preached at the Independent Schoolhouse on Main Street in Ridgefield. In the 1840s, a second meetinghouse in town was built, and the congregation grew. A third church and rectory were built on Main Street in 1884. When a large Main Street estate was available for a new, stately building, the congregation jumped at the opportunity, and hired ecclesiastical architect Harold Wagoner to design a refined, Colonial Revival style church, which was built in 1965. Executed in brick, the church has great verticality, created by the colossal columns supporting its pedimented portico and the spire that rises over an open belfry to a height of 149 feet. Set back from the street, the church still has a commanding presence.

Ridgefield Train Depot // 1870

In 1870, the Ridgefield Branch branch line of the Danbury and Norwalk Railroad and later the New York, New Haven and Hartford Railroad was built connecting the sleepy village of Ridgefield to Branchville train station via the main line. The line was an early risk, built to offer service to the wealthy New Yorkers who began arriving to spend their summers in Ridgefield. Many of these “summer people” had their own private railroad cars, with chauffeurs meeting them as they arrived, driving horse and buggies to bring them and their luggage to their estates located throughout the town. As travel shifted to personal automobile, ridership dropped in the early 20th century, and the branch was replaced by bus service in 1925. Freight service was scarce, and lasted longer, to 1964. The depot was sold to the Ridgefield Supply Company, who used the 1870 building as storage for decades until it was disassembled, moved and rebuilt by the Ridgefield Supply Company in 2015, as part of their expansion. The historic station today provides an important link to Ridgefield’s past.

Ridgefield Public Library // 1901

The Ridgefield Public Library is an intriguing Beaux Arts style building from the turn of the 20th century. Built in 1901, the brick structure replaced the Smith Tavern, a 1798 frame structure built by Amos Smith right on Main Street. In 1900 the Smith Family sold the property to James N. Morris who had this library built in memory of his wife, Elizabeth, donating it to the town. Architect Raleigh G. Gildersleeve is credited with the design which is comprised of a one-story building constructed of brick with cast stone trim details and ironwork at the door. The library was given later additions, which are recessive in location and detailing to let the original building shine, as it should!

Ridgefield Town Hall // 1896

Ridgefield, Connecticut was settled in 1708 when 24 families from Long Island purchased land from Chief Catoonah of the Ramapo tribe. The Fundamental Orders adopted by Connecticut in 1639 directed would-be settlers, able to support a minister, to establish a settlement, build a Congregational church and farm the land. This is exactly what was done in Ridgefield, beginning in 1708. The original 24 proprietors received 7½-acre home lots drawn by lottery, with a 25th reserved for the minister. The lots were located up and down Main Street from a Common where a Meeting House was built. The town grew and for much of its three centuries, was primarily comprised of old farms. By the late 19th century, spurred by the connection of the railroad, Ridgefield was “discovered” by wealthy New York residents, who assembled large estates in town, a trend that has only picked up in the 21st century! Population growth and a large fire on the town’s Main Street in 1895 necessitated a new Town Hall building. The present Town Hall building was constructed in 1896 from plans by architect Philip Sunderland. Colonial Revival and Romanesque in style, the two-story brick building features a pedimented central bay also containing the entrance with fan light transom, round arched windows, brownstone trim, and narrow pilasters of brick. The building houses town offices today.